36950-98-8

Upstream product

• 40110-96-1 4'-benzyloxy-5,6,7,8-tetramethoxyflavone 
• 481-53-8 tangeritin 
• 1350827-37-0 2-(4-benzyloxybenzoyloxy)-3,4,5,6-tetramethoxyacetophenone 
• 3162-28-5 2-hydroxy-3,4,5,6-tetramethoxyacetophenone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1486-50-6 4-(benzyloxy)benzoic acid chloride 
• 85374-52-3 1-(4-benzyloxyphenyl)-3-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)propane-1,3-dione 
• 73898-14-3 4'-benzyloxy-5,6,7,8-tetramethoxyflavanone 
• 40110-95-0 4-benzyloxy-2'-hydroxy-3',4',5',6'-tetramethoxychalcone 
• 4397-53-9 p-benzyloxybenzaldehyde 

Downstream Products

• 16545-23-6 xanthomicrol 
• 6959-55-3 Acetic acid 4-(5,6,7,8-tetramethoxy-4-oxo-4H-chromen-2-yl)-phenyl ester 
• 481-53-8 tangeritin 
• 2798-20-1 gardenin B 

Relevant academic research and scientific papers

Tangeretin inhibits the proliferation of human breast cancer cells via CYP1A1/CYP1B1 enzyme induction and CYP1A1/CYP1B1–mediated metabolism to the product 4′ hydroxy tangeretin

Tangeretin is a polymethoxylated flavone with multifaceted anticancer activity. In the present study, the metabolism of tangeretin was evaluated in the CYP1 expressing human breast cancer cell lines MCF7 and MDA–MB–468 and in the normal breast cell line M

Synthesis of Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity

[Figure not available: see fulltext.] A series of polymethoxyflavonoids were synthesized via cleavage of the glycosidic bond, dehydrogenation, selective methylation, bromination, nucleophilic aromatic substitution, O-prenylation, Claisen–Schmidt aldol condensation, cyclization, and oxidation from very abundant and inexpensive natural flavonoids hesperidin and naringin. The in vitro antiproliferative activity of the synthesized compounds was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2, and SUN-5) by the CellTiter-Glo assay. The results showed that some of synthesized compounds exhibited moderate to high antiproliferative activity. Among them, (2E)-1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-en-1-one was revealed to be the most active with IC50 values ranging from 10.35 to 13.89 μM against all four cancer cell lines, the IC50 value (10.35 μM) being below positive control cisplatin (12.36 μM) against HepG-2 cells.

Analysis of Fluorescence Spectra of Citrus Polymethoxylated Flavones and Their Incorporation into Mammalian Cells

Citrus polymethoxylated flavones (PMFs) influence biochemical cascades in human diseases, yet little is known about how these compounds interact with cells and how these associations influence the actions of these compounds. An innate attribute of PMFs is their ultraviolet-light-induced fluorescence, and the fluorescence spectra of 14 PMFs and 7 PMF metabolites were measured in methanol. These spectra were shown to be strongly influenced by the compounds' hydroxy and methoxy substituents. For a subset of these compounds, the fluorescence spectra were measured when bound to human carcinoma Huh7.5 cells. Emission-wavelength maxima of PMF metabolites with free hydroxyl substituents exhibited 70-80 nm red shifts when bound to the Huh7.5 cells. Notable solvent effects of water were observed for nearly all these compounds, and these influences likely reflect the effects of localized microenvironments on the resonance structures of these compounds when bound to human cells.

Regioselective hydroxylation of diverse flavonoids by an aromatic peroxygenase

Aromatic peroxygenases are extracellular fungal biocatalysts that selectively oxidize a variety of organic compounds. We found that the peroxygenase of the fungus Agrocybe aegerita (AaeAPO) catalyzes the H 2O2-dependent hydroxylation of diverse flavonoids. The reactions proceeded rapidly and regioselectively yielding preferentially monohydroxylated products, e.g., from flavanone, apigenin, luteolin, flavone as well as daidzein, quercetin, kaempferol, and genistein. In addition to hydroxylation, O-demethylation of fully methoxylated tangeretin was catalyzed by AaeAPO. The enzyme was merely lacking activity on the quercetin glycoside rutin, maybe due to sterical hindrance by the bulky sugar substituents. Mechanistic studies indicated the presence of epoxide intermediates during hydroxylation and incorporation of H2O2-derived oxygen into the reaction products. Our results raise the possibility that fungal peroxygenases may be useful for versatile, cost-effective, and scalable syntheses of flavonoid metabolites.

B-Ring-modified and/or 5-demethylated nobiletin congeners: Inhibitory activity against pro-MMP-9 production

Three metabolites and 12 analogues of nobiletin (1) were synthesized. Whereas nobiletin derivatives 2-4 inhibited pro-MMP-9 production similarly in both PMA- and TNF-α-stimulated human lens epithelial cells, the 2′-hydroxylated analogue 5a exerted marked inhibitory effects (IC 50: 0.4 μM) on PMA-treated cells, which were 170-fold more potent than those on TNF-α-treated cells. This activity may be closely related to PKC-mediated transcriptional regulation of pro-MMP-9.

Semisynthesis and antiproliferative evaluation of a series of 3′-aminoflavones

A series of 3′-aminoflavones 5,6,7,8-tetra- or 5,7-dioxygenated on the A-ring was synthesized from tangeretin or naringin, two natural Citrus flavonoids. These flavones were evaluated for antiproliferative activity, activation of apoptosis, and inhibition

Biotransformation of polymethoxylated flavonoids: Access to their 4′-O-demethylated metabolites

Regioselective O-demethylation of the flavones tangeretin (1) and 3-hydroxytangeretin (6) into their 4′-O-demethylated metabolites was performed by using an Aspergillus niger strain. This method serves as a straightforward alternative to multistep synthes

Inhibitor of aldose reductase

An inhibitor of aldose reductase which contains, as the effective ingredient, a flavone derivative having the following formula: STR1 wherein R1 is hydrogen atom or hydroxyl group, R2 is hydroxyl group or methoxyl group or a pharmace